


Taking Risks

by LoverAwakened



Category: Supernatural
Genre: Bathroom Sex, Bottom Castiel, Bottoming from the Top, Drunk Dancing, Drunk Texting, First Dance, First Kiss, First Time, Fluff and Smut, Friends to Lovers, Gay Bar, M/M, Oral Sex, Season/Series 12, Sex in the Impala, Top Dean Winchester
Language: English
Status: Completed
Published: 2017-07-12
Updated: 2017-07-12
Packaged: 2018-12-01 07:40:51
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,803
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11481744
Author URL: https://archiveofourown.org/users/LoverAwakened/pseuds/LoverAwakened
Summary: Dean gets drunk at a gay bar and texts Cas to meet up with him. After thirty minutes of back and forth texting, Castiel reluctantly enters the bar. The angel has never been to a gay bar nor has he ever danced before. Tonight, however, those two things will not be Castiel's only firsts.





	Taking Risks

**Author's Note:**

  * For [anyrei](https://archiveofourown.org/users/anyrei/gifts), [mugglerock](https://archiveofourown.org/users/mugglerock/gifts).



> Narrative inspired by and based on this [tumblr post](https://the-real-anyrock.tumblr.com/post/162662840750/choose-your-own-ending) from [the-real-anyrock](https://the-real-anyrock.tumblr.com/) ([anyrei](http://archiveofourown.org/users/anyrei/pseuds/anyrei) and [mugglerock](http://archiveofourown.org/users/mugglerock/pseuds/mugglerock)) that I have since dubbed the AnyRock Challenge. These two are amazing authors, my absolute favorite, and I had so much fun putting this story together!

Dean waited another five minutes before he decided to walk out of Bam Bam’s and drag the angel into the bar himself. The pungent aroma of alcohol, cigarettes, and vomit hit Dean like a slap to the face. He gagged on the stench. It had been nearly an hour since he’d had another drink, deciding to wait for Cas, and he was nowhere near drunk enough anymore to deal with the scents accompanying a night of bad decisions. 

Dean walked past a couple of drunk chicks making out on a parking block. The redhead had her fingers tangled in the brunette’s hair cradling the back of her head. Any other time the hunter would have stopped to appreciate the view, but Dean was determined to find the angel. 

He scanned the parking lot looking for Cas’ familiar vehicle but it seemed to be eluding him. Dean’s stomach turned sour at the thought of Cas changing his mind and taking off. He felt the sting of tears behind his eyes as he turned back toward the bar.  _Do not cry, damn it. You’re a man, not a little bitch._ He dug his palms into his eyes, desperately trying to rub the stinging away. 

When Dean reached for the door, a yellow cab idling off to the side of the building caught his eye. Slowly, Dean made his way over and glanced in the backseat of the cab. A wave of relief washed over Dean as he saw the angel in the back, elbows propped on his knees, hands raking through the dark strands of hair making them stick up in adorable little tufts. Dean smiled and tapped on the window, chuckling as the angel startled. Cas rolled down the window, giving Dean a tense smile. 

“Hello, Dean.” 

“Heya, Cas. Whatcha doing out here. By yourself. In the back of a cab?” He raised his eyebrows in question and Cas did his cute eye-squinty-head-tilt thing. 

 

Castiel sat back and sighed, nervously fisting the fabric of his trench coat. “We’re thirty minutes from the bunker, Dean, and I was going to drive you home, remember?” As an afterthought, he added, “Did you think I was texting you the entire time while I was driving, Dean? That’s very dangerous.” Castiel scolded. 

“I thought you were coming to get drunk with me, Cas?” Dean pouted. 

“I said I would drink with you, Dean, but I believe I should avoid getting ‘wasted’.” 

Dean did a full body laugh, opening the door of the cab. “Man, you’re still doing the finger quotes. That’s precious,” He teased, “C’mon Cas, let’s go. I told you there was a motel about a block away. Don’t worry about getting ‘wasted’.” 

Dean mimicked the angel’s finger quotes still laughing. Castiel scowled at him and hit Dean on the shoulder. The angel paid the cab driver and followed Dean into Bam Bam’s. It did seem to be a homosexual bar, as every couple Castiel saw on the dance floor, seated at the tables, and along the bar were all same-sex couples. He walked fairly close behind Dean, noticing a few other bar patrons checking the elder Winchester out and he instantly felt a spark of jealousy before immediately tamping it down. He and Dean were friends. Castiel had no claim over him. If Dean wanted to dance or drink or even go to the motel with someone else, Castiel was not going to stand in the way. Dean deserved some happiness, even a fleeting thing like a one-night stand. 

Dean sat at the bar ordering six of something, gesturing for Castiel to sit down in the empty seat beside him. The bartender came back with a bottle of whiskey and six empty shot glasses he lined up in a row. The bartender looked at Dean in question as he poured the last shot. 

“They’re not all for me, Tom, promise.” Dean purred, winking at the bartender, quite obviously flirting with the man. 

 _He’s not yours. He’s not yours. He’s not yours._  The angel glanced around the bar. He didn’t know how to behave around Dean now. All of this was so much easier via text, Castiel thought. He didn’t know how he was going to handle being face to face with Dean after the things they had discussed on the phone. Castiel needed to keep his wits about him so that he didn’t embarrass himself and more importantly, didn’t lose Dean’s friendship.

Dean slid one shot glass in front of himself, moving the other five in front of the angel. Castiel quirked his brow, but the hunter only shrugged in response. 

“You got some catching up to do,” Dean explained. 

Castiel’s eyes went wide as he took in the shots in front of him. Taking a deep breath, the angel downed all five shots with lightning speed. Dean hadn’t even got his glass to his lips yet. 

“Holy shit, Cas!” Dean rasped. He finished his shot and leaned in to whisper in Cas’ ear. “Hey, see that other bartender down on the end? The chick with half her head shaved and metal all over her face?” 

The angel nodded, beginning to feel the effects of the alcohol he just consumed. 

“She hasn’t seen you yet, so run down there and order five more shots from her.” 

“But I just had five!” Castiel squeaked.

“And you need to catch up, Mr. it-takes-a-whole-liquor-store-to-get-me-drunk.” 

“Dean, I told you, my grace— “ 

“Yeah, yeah. I know. Grace is on the fritz. Just go do it. For me. Please!” Dean pleaded sweetly, batting those ridiculously long blonde lashes. 

“Fine,” Castiel huffed, giving in. As if he would ever deny the hunter of anything. “I’ll be right back.” 

When Castiel returned, Dean was sipping on a beer. 

“Sooooo, how ya feelin’?” 

“My chest is very warm and my limbs are tingling,” Castiel replied. 

“Awesome, you’re buzzed!” 

“Buzzed?” 

“Yeah, let’s go dance, now that I’m not falling over drunk anymore.” 

Dean tried to pull him over to what passed for a dance floor in this place, but Cas remained firmly rooted to where he stood. He had that terrified look on his face that he had at the brothel Dean took him to so many years ago. 

“Cas?” 

The angel swallowed, shifting from foot to foot. “I-I don’t know how to d-dance, Dean.” He confessed, eyes lowering to the floor, embarrassed. 

“It’s all right, Cas, you just move your body to the rhythm of the music. I’ll show you.” Dean began pulling off the angel’s coats and tie. 

“What are you doing?” 

“Humans don’t dance in layers.” Dean removed the trench coat, suit jacket, and tie and set them on the barstool. Then he unbuttoned Cas’ collar and cuffs and untucked the angel’s dress shirt, all while Cas stood perfectly still, like a giant dress-up doll. 

“That’s better, now, c’mon.” 

Dean grabbed the angel’s hand once again, leading him to the dance floor. The music was shitty and loud, the bass reverberating through his bones, but he was determined to show Cas a good time. Dean showed Cas how to roll his shoulders and move his arms to the music, the angel’s hips moving in small figure-eights to the beat. 

When the angel realized that neither Dean nor the others at the bar were laughing at him, he began to loosen up; body moving freely and silly, smile lighting up his face. Several people came to talk to them, all of them taking an interest in Cas. Dean smiled wickedly at the angel, winking, and Cas tilted his head in confusion. 

“You know,” Dean said, eyeing the two guys grinding against each other next to Cas, “he’s never been to a gay bar before. Hell,” Dean added, gripping the angel tightly by the hips, “this is his first time dancing, dude never even danced before. Isn’t he doing great?” 

Cas shot Dean a worried glance, but the hunter just smiled brightly at him. The surrounding people on the dance floor were eating it up, all  _aw_ ’s and  _oooh_ , and  _wow really_ ’s. 

“Yeah, he’s from a religious family,  _super_  strict on rules.” Dean smirked as Cas pinned him with an icy glare.

And that was the final nail in the coffin. Everyone started buying Cas shots and asking the angel to dance. He looked at Dean for guidance but Dean just laughed, nodding at one of the guys who asked Cas to dance with him. 

“Go have fun man, I’m right here with you.” 

The drinks kept flowing and they kept dancing, Cas currently between two giggling girls, the redhead and brunette from the parking lot earlier. Cas’ hands were on the brunette’s waist, one leg between hers, and they were rolling their hips together in a slow, dirty grind. The redhead pressed against Cas’ back, dainty hands roaming underneath the white dress shirt which had somehow been unbuttoned a few more buttons revealing the angel’s flushed, sweaty chest. It was so hot, watching Cas with those girls. Dean could feel his jeans becoming uncomfortably tight. 

He thought back to their text messages from earlier. Did he want to risk sex with someone he cared about? Especially when that someone was Cas; his best friend and guardian angel. 

Cas was soaked in sweat and he shook his hair out like a dog, causing an uproar of laughter from the girls. The dark strands were sticking out at all angles, his skin flushed pink from the alcohol and exertion of dancing. His shirt stuck to the muscles of his arms and abdomen.  _Yes, I can absolutely risk it_. Dean downed his shot and wiped the back of his hand across his mouth. 

“Mind if I cut in ladies?” Dean asked, waggling his eyebrows and snaking an arm around the angel’s lower back. 

“Sure! Thanks for the dance, Castiel!” The brunette giggled, walking off hand-in-hand with the redhead. 

Castiel was a little unsteady on his feet, probably due to the large quantity of alcohol the angel had consumed. He threw his arms around Dean’s neck, face lit up with a huge smile, blue eyes twinkling. Dean’s body was all hard angles and muscle and Castiel couldn’t remember anything feeling quite so good.

“I’m having an extraordinary amount of fun, Dean. Thank you for inviting me out.” 

Castiel’s eyes kept drifting down to Dean’s lips. Those full, pink lips. Not for the first time, the angel wondered what those lips would taste like. Dean laced his fingers through Castiel’s sending a jolt along the angel’s nerves. 

“C’mere.” 

Dean pulled Cas through the crowd, towards the men’s room. Why were they headed to the restroom? 

“Do you need assistance using the restroom, Dean?” 

Cas’ brow furrowed and Dean chuckled at the angel’s innocence. He pushed through the heavy door of the men’s room, checking each stall to make sure they were alone. Once he was satisfied that they were by themselves, Dean locked the bathroom door behind Cas. 

“Um, Dean?” 

The angel’s voice cracked and Dean found the sound arousing. Leaning in, Dean pressed his lips gently to his friend’s. Despite being perpetually chapped, Cas’ lips were warm and soft. He brought a hand up to Cas’ face, deepening the kiss. The groan that rumbled from the angel’s throat lit Dean’s blood on fire. He backed Cas up against the wall and licked his way into the angel’s mouth again. Cas tasted warm and sweet, like whiskey and honey. He rolled his hips, grinding his erection into Cas, pleased to feel the hard outline of the angel’s own erection. 

“Oh, Cas,” Dean moaned, hands fumbling with the other’s belt buckle as he assaulted Cas’ mouth with another deep kiss, tongue plunging in and out in a filthy rhythm. “Taste so good,” he mumbled, “Fuck, Cas, wanted to do this for so long. So long.” Dean sank to his knees pulling Cas’ pants and boxers down with him. 

“D-dean, what are you doing?” 

“Trying something.” 

Dean stared at Cas’ cock. It was long and slim and utterly perfect, the head flushed bright pink, a fat drop of precome beaded at the tip.  _Go big or go home, right?_ Dean darted his tongue out to lick away the precome and Cas hissed above him. Then he swallowed Cas down in one go, hollowing his cheeks, sliding his mouth up and down rapidly on the angel’s cock. 

“Fuck, Dean!” Cas screamed, hands shooting out to bury themselves in the hunter’s hair. 

Dean groaned around a mouthful of angel cock. Cas swearing was all sorts of hot and his own dick twitched in response.

“Dean,” Castiel whined, trying to stop himself from rocking into the wet heat of the hunter’s mouth. He could feel his release building but he couldn’t find the words to warn Dean. His whole existence was focused on the pleasure he felt between his legs. And just when Castiel was about to ejaculate, he tightened his fist in Dean’s hair, yanking Dean off his penis. In retrospect, he probably should have released the hunter’s hair, because thick spurts of white shot all over Dean’s face, having essentially been held in place by Castiel’s hand. 

Dean stared at Castiel from his position kneeling at the angel’s feet, the green of his irises a thin ring surrounding blown black pupils. And even though the angel was spent, his come dripping down Dean’s cheeks, lips, and chin, made Castiel feel the stir of desire in his gut once more. 

“Oh, Dean, I-I’m so sorry! Here, let me help you clean that up.” He touched two fingers to the hunter’s forehead and all the ejaculate disappeared. Dean hadn’t spoken, still on his knees and staring up at the angel. The silence was making Castiel nervous. 

“Dean?” 

Dean stood, lunging at the angel, crashing his lips with Castiel’s as he lifted him up by the backs of his thighs and pressed the angel into the wall. Castiel wrapped his legs around the hunter’s waist. Dean tasted wonderful and his body felt exquisite against his own. Castiel could absolutely get used to this. A voice in the angel’s mind whispered that Dean was drunk and in the light of day, he’d want nothing to do Castiel. Dean would never want to pursue a romantic relationship because he was too afraid to lose the angel as a friend.  _This is a one-time only thing._  Castiel forced the negative thoughts to the back of his mind, focusing instead on the feel of Dean’s strong muscles holding him up and the mouth sucking marks on his exposed skin. 

Dean’s kiss was passionate. Sloppy and unyielding. The two men swallowed each other’s moans, panting into each other’s mouths as they tried to catch their breath between kisses. Dean mumbled the angel’s name repeatedly. He was hard and leaking in his jeans, but he was getting older and as much fun as dirty bathroom sex was, they should probably go find a room.

“Let’s get out of here,” Dean suggested and Cas nodded, following the hunter out of the bar. 

The night air was thick and heavy, humid from the storm clouds rolling in that threatened to rain down. 

“The motel’s this way,” 

Dean hooked his thumb in the direction of the motel, grabbing Cas’ hand, but the angel remained unmoving. Trying to get an angel to budge when they didn’t want to move was about as easy as trying to push a building over with your bare hands. 

“What is it, Cas?” 

The angel looked over to where the Impala was parked. Most of the other cars were gone from the lot, being that they did Last Call while Dean and Cas were  _occupied_  in the bathroom, so it was easy to spot the Chevy, parked under a street lamp several rows back. 

“No, nuh-uh. We are both way too hammered to be driving anywhere.” 

The angel sighed and the bastard actually rolled his eyes at Dean. Cas tugged a complaining Dean all the way to the Impala, spinning him around and pressing his back against the cool metal of the car. Cas snaked Dean’s keys from his pocket, unlocking the car and throwing his coats and tie in a balled-up pile on the passenger seat. He then pressed his body back up against Dean, biting and licking at the hunter’s neck, hands exploring Dean’s body underneath his clothes. 

Dean groaned, still hard from not getting to come in the bathroom. He was about to suggest they run to the motel and grab a bed so they could get down to business, but apparently, Cas had other plans. 

The angel tongued Dean’s ear and nibbled on his earlobe, deep gravel voice rasping in his ear. 

“I want you to fuck me, Dean.” 

Dean froze, staring at his friend with wide, shocked eyes. 

“I want you to fuck me in the backseat of this car. Now, Dean.” 

Cas bit down on Dean’s lower lip, grabbing Dean’s crotch and the hunter thought he was going to come in his pants like a teenager.  _Baseball, Sam in a dress, Mom naked… okay, okay I’m good now, I’ll be fine._

“Do you know how many times I’ve thought about riding you, Dean? In every room in the bunker. In the backseat of Baby. The front seat. On Baby’s hood.” 

_Fuck, not good, I’m not good._

“Cas,” Dean groaned, “stop talking or you’re gonna make me come.” He whined. 

Cas arched his brow. “You could come just from my voice?” He smirked, “We’ll have to try that sometime.” 

Cas opened the door to the backseat and pushed Dean in by the head. He landed, sprawled on his back and Cas crept over him predatorily. The angel took off his shirt, slowly sliding the black slacks down, while Dean ripped his clothes off in record speed, adding it to the growing pile of clothing in the front seat. 

Once they were both naked, Cas took a moment to let his gaze roam over Dean’s body. The hunter was slightly embarrassed. Sure, he kept in shape due to the nature of the job, but where Cas’ belly was flat, sharp angles of hip bones sticking out, Dean’s belly was soft and slightly rounded. He didn’t think he was fat or anything, but he definitely wasn’t cut like he used to be in his early twenties. 

“You’re beautiful,” Cas whispered, causing a blush to rise to Dean’s cheeks that had nothing to do with alcohol. 

“Thought you were gonna ride me,” Dean deflected, not comfortable with the praise of his body. 

Cas’ eyes darkened and he positioned his knees on either side of Dean’s hips. 

“Don’t we need to do stuff first?” Dean worried. He tried to remember any gay porn he’d ever seen but his brain was fogged over from the whiskey. Dean wasn’t an expert in gay sex, but he was pretty sure it involved more than just shoving his dick in the hole.

“You won’t hurt me, Dean.” Cas assured and the angel reached behind himself and Dean could swear he saw a faint glowing before Cas lined Dean up and lowered himself slowly on Dean’s cock. 

“Wait, we need—ah!” 

Dean lost his ability to breathe as Cas’ tight, hot channel squeezed around him. Then he felt an extraordinary amount of wetness and he  _knew_  they didn’t use any lube. 

“Dude, are you wet?!” Dean asked, incredulous. 

Cas stilled his movements, chuckling softly. “I do not ‘self-lubricate’, Dean. I merely used my grace to aid in penetration for intercourse.” 

“Your grace that’s on the fritz. That grace?” 

Cas looked sheepish. “Perhaps I got a bit carried away with the lubrication.” 

“Fair enough. For future reference, though, dude, don’t say things like ‘self-lubricate’ or ‘penetration’ or ‘intercourse’ when you’re riding my dick.”

They both laughed and Dean pulled Cas into a slow, deep kiss. Dean rolled his hips up, meeting every downward thrust from the angel above him. It was amazing. It was incredible. This was so much more than sex. Cas sat up, rolling those sinful hips and braced his hands on Dean’s chest and Dean didn’t know how he was ever going to have sex with anyone else ever again, knowing that sex with Cas felt this spectacular. Dean was ruined. Cas threw his head back and panted, a look of pure bliss on the angel’s face. 

“Dean,” Cas growled out, spilling onto Dean’s chest. 

And that gravelly voice, growling out his name, tipped Dean over the edge, his own release shooting deep inside the angel.  _His_  angel. 

Cas cleaned them up with his mojo and the two dressed in silence. Dean rolled all the windows down to allow fresh air through the car and hopefully take the sweaty stench of sex with it. Not that he didn’t love what happened, but he had a little brother that rode in this car often and Dean did  _not_  want to deal with Sasquatch’s attitude. 

Dean laid down in the backseat propped up against the door and spread his legs to allow Cas to lay down and lean back against his chest. Wrapping the angel tight in his arms Dean sighed, feeling content for the first time in a long while. The rumble of thunder overhead was oddly soothing as they lay in the Impala, listening to each other breathing. The humidity had vanished and the temperature dropped, suddenly, a chill in the air making Dean shiver.

“Dean… we need to— “ 

The clouds opened and rain poured down, soaking everything in its path instantaneously. 

“Shit!” 

Dean knocked Cas off his lap, the angel grumbling as Dean struggled to get the Impala’s windows rolled up. 

“Fuck, hurry before my Baby gets soaked!” 

Cas helped Dean get the windows up and, both agreeing that they didn’t want to be trapped in the car til they were sober, made a break for the motel on foot, running the block and a half in the pouring rain. By the time they stumbled into the motel room, they looked like a couple of drowned rats. Dean laughed so hard his sides hurt. Dripping, they stripped out of their wet clothing, hanging them in the bathroom to dry before pulling back the covers of the queen size bed and crawling in together, naked. 

Cas sighed happily, curling up in Dean’s arms and fitting his head underneath Dean’s chin. His hair was plastered to his head, but the angel still looked adorable. Between all the hours Dean had been awake, the alcohol, and the crazy-hot sex, Dean was exhausted. As he drifted off to sleep with his angel in his arms, Dean suddenly worried that come morning, everything would change. 

 _Oh, well, I’ll worry about that when I wake up._  Dean pressed a kiss to the top of Cas’ head and pulled him tighter to his body. 

“Goodnight, Angel.”

**Author's Note:**

> Follow me on Tumblr [LoverAwakened](http://www.lover-awakened.tumblr.com)


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